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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-07-23 05:44:50 UTC |
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HMDB ID | HMDB0001263 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Allysine |
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Description | Allysine, also known as 6-oxonorleucine or alpha-aasa, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Allysine is a very strong basic compound (based on its pKa). Allysine exists in all eukaryotes, ranging from yeast to humans. Within humans, allysine participates in a number of enzymatic reactions. In particular, allysine and L-glutamic acid can be biosynthesized from saccharopine; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In addition, allysine can be converted into aminoadipic acid; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In humans, allysine is involved in lysine degradation. Allysine is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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2-Amino-5-formylvaleric acid | ChEBI | 2-Aminoadipate 6-semialdehyde | ChEBI | 6-Oxonorleucine | ChEBI | alpha-Aminoadipic acid delta-semialdehyde | ChEBI | alpha-Aminoadipic delta-semialdehyde | ChEBI | HCO-[CH2]3-CH(NH2)-COOH | ChEBI | 2-Amino-5-formylvalerate | Generator | 2-Aminoadipic acid 6-semialdehyde | Generator | a-Aminoadipate delta-semialdehyde | Generator | a-Aminoadipic acid delta-semialdehyde | Generator | alpha-Aminoadipate delta-semialdehyde | Generator | Α-aminoadipate δ-semialdehyde | Generator | Α-aminoadipic acid δ-semialdehyde | Generator | a-Aminoadipic delta-semialdehyde | Generator | Α-aminoadipic δ-semialdehyde | Generator | a-Aminoadipate δ-semialdehyde | HMDB | a-Aminoadipic acid δ-semialdehyde | HMDB | a-Aminoadipic δ-semialdehyde | HMDB | (2S)-2-Amino-6-oxohexanoate | HMDB | (2S)-2-Amino-6-oxohexanoic acid | HMDB | 2-Amino-hexanedioate | HMDB | 2-Amino-hexanedioic acid | HMDB | 2-Amino-hexanedioic acid semialdhyde | HMDB | 2-Aminoadipate semialdehyde | HMDB | 2-Aminoadipate-6-semialdehyde | HMDB | 5-Formyl-norvaline | HMDB | 6-oxo-L-Norleucine | HMDB | 6-oxo-Norleucine | HMDB | alpha-Aminoadipic semialdehyde | HMDB | L-2-Aminoadipate 6-semialdehyde | HMDB | L-6-Oxonorleucine | HMDB | L-Allysine | HMDB | 2-Aminoadipic semialdehyde | HMDB | alpha-AASA | HMDB | alpha-Aminoadipate semialdehyde | HMDB |
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Chemical Formula | C6H11NO3 |
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Average Molecular Weight | 145.1564 |
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Monoisotopic Molecular Weight | 145.073893223 |
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IUPAC Name | 2-amino-6-oxohexanoic acid |
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Traditional Name | allysine |
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CAS Registry Number | 1962-83-0 |
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SMILES | NC(CCCC=O)C(O)=O |
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InChI Identifier | InChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10) |
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InChI Key | GFXYTQPNNXGICT-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alpha amino acids |
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Alternative Parents | |
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Substituents | - Alpha-amino acid
- Medium-chain fatty acid
- Amino fatty acid
- Fatty acyl
- Fatty acid
- Alpha-hydrogen aldehyde
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Aldehyde
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Primary aliphatic amine
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Amine
- Organic oxygen compound
- Organic nitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9100000000-e7c5c166681ba0316b25 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-8910000000-8fb215d3dd09e5553352 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ufs-2900000000-cc3c3ade4cefc6b57880 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ue9-9700000000-1f5f0f3378ed80283ec8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0abc-9000000000-dd87ab890dceec9e01cb | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-5623b839bf292d641b92 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-4900000000-7473bdea5b2f626515f1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-12c42805d877e4f712b6 | JSpectraViewer |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | <0.2 uM | Infant (0-1 year old) | Not Specified | Normal | | details | Urine | Detected and Quantified | <1 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected and Quantified | 1.6-28 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Pyridoxine dependency with seizures (PDE) | | details |
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Associated Disorders and Diseases |
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Disease References | Pyridoxine-dependent epilepsy |
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- Plecko B, Paul K, Paschke E, Stoeckler-Ipsiroglu S, Struys E, Jakobs C, Hartmann H, Luecke T, di Capua M, Korenke C, Hikel C, Reutershahn E, Freilinger M, Baumeister F, Bosch F, Erwa W: Biochemical and molecular characterization of 18 patients with pyridoxine-dependent epilepsy and mutations of the antiquitin (ALDH7A1) gene. Hum Mutat. 2007 Jan;28(1):19-26. [PubMed:17068770 ]
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Associated OMIM IDs | - 266100 (Pyridoxine-dependent epilepsy)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB010644 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 202 |
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KEGG Compound ID | C01475 |
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BioCyc ID | Not Available |
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BiGG ID | 1445244 |
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Wikipedia Link | Allysine |
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METLIN ID | 6118 |
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PubChem Compound | 207 |
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PDB ID | Not Available |
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ChEBI ID | 17027 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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